baloxavir marboxil   Click here for help

GtoPdb Ligand ID: 11748

Synonyms: S-033188 | S033188 | Xofluza®
Approved drug
baloxavir marboxil is an approved drug (Japan & FDA (2018), EMA (2021))
Compound class: Synthetic organic
Comment: Baloxavir marboxil is an orally delivered anti-influenza virus drug. It is a prodrug that is converted to baloxavir [1]. Mechanistically baloxavir is a first-in-class inhibitor of the cap-endonuclease (CEN) activity of an acidic protein within the viral polymerase complex [3] that is essential for viral gene transcription and replication. Alternative influenza antivirals (e.g. oseltamivir, peramivir and zanamivir) target the neuraminidase enzyme that is required for fusion and entry of virus into the host cells, and the budding process that releases newly synthesised virions.
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 7
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 124.84
Molecular weight 571.12
XLogP 4.13
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES COC(=O)OCOc1c(=O)ccn2c1C(=O)N1CCOC[C@H]1N2[C@@H]1c2ccccc2SCc2c1ccc(c2F)F
Isomeric SMILES COC(=O)OCOc1c2C(=O)N3CCOC[C@H]3N(n2ccc1=O)[C@H]1c2c(CSc3ccccc13)c(c(cc2)F)F
InChI InChI=1S/C27H23F2N3O7S/c1-36-27(35)39-14-38-25-19(33)8-9-31-24(25)26(34)30-10-11-37-12-21(30)32(31)23-15-6-7-18(28)22(29)17(15)13-40-20-5-3-2-4-16(20)23/h2-9,21,23H,10-14H2,1H3/t21-,23+/m1/s1
InChI Key RZVPBGBYGMDSBG-GGAORHGYSA-N
Bioactivity Comments
Bioactivity is associated with the active metabolite baloxavir (S-033447). Baloxavir inhibits Influenza A-induced death of MDCK cells in vitro with an EC50 of 0.9 nM [2].